Manufacture of sodium arylamins.



UNITED STATES PATENT OFFICE.

OTTO LIEBKNECHT, OF FRANKFORT-ON-THE-MAIN, GERMANY, ASSIGNOR TO DEUTSCHEGOLD- & SILBER-SCHEIDEANSTALT VORM. ROESSLER, OE FRANKFORT-ON-THE-MAIN,

GERMANY.

MANUFACTURE OF SODIUM ABYLAMINS.

Specification of Letters Patent.

Patented Nov. 10, 1908.

Application filed June 3, 1908. Serial No. -136,421.

To all whom 'it may concern:

Be it known that I, O'r'ro LIEBKNECHT, a

' subject of the Emperor of Germany, and a resident of Frankfort on theMain, Germany, have invented certain new and useful.

Improvements in the Manufacture of Sodium Arylamins, of which thefollowing is a specification.

Sodium has no perceptible action on anilin, even if both bodies be keptin contact with each other for several days and be energeticallystirred, at the boiling point of anili'n. Sodium behaves in the samemanner towards other arylamins, such, for instance,-asmono-methyl-anilin, toluidin, and the like.

' The preparation of sodium arylamins by the direct action of sodium onanilin has therefore not hitherto been practicable.

I have discovered that sodium will combine smoothly with the aforesaidaromatic bodies and hydrogen be evolved, if the reaction be effected 1nthe presence of a small 4 amount of a catalytic substance such forinstance as copper, a copper oxid, a copper salt, or nickel, or cobalt,or an oxid, or a salt, of nickel, or of cobalt, or other heavy metal, oran oxid or a salt thereof.

The combination can be effected at a comparatively low temperature; assodium reacts violently on amlin at a temperature as low as 140centigrade, if a catalytic substance be used.

The following are examples, of how the invention may be performed but itis not limited to these examples. The parts-are by weight. v

Example I. 300 parts of anilin are heated to 140 centigrade and aboutfrom 0.1 to 0.2 of a part of nickel oxid is added and then 45 parts ofsodium are added in several portions, at a time care being taken toawait the end of the reaction of a precedin portion before adding afurther portion 0 sodium. Hydrogen is evolved and sodium-anilinisformed. The sodium-anilin can be separated in the usual manner from theexcess of anilin.

Example II. 400 parts of ortho-toluidin are heated to about 175centigrade, about 0.2 ofa part of copper carbonate is added, and then,while stirring, 30 parts of sodium are added in portions at a time asstated in Example IV. 400 parts of asymmetric meta-xylidin are heated toabout 200 centigrade, about 0.5 of a part of copper-carbonate is addedand then while stirring 40 parts of sodium are added in portions.Hydrogen is evolved and asymmetric meta-xylidin-sodium is formed and canbe separated in the usual manner from the excess of asymmetricmeta-xylidin.

Eample V. 200 parts of mono-methylaiiie lin are heated to boiling pointwith 0.2 of a part of cobalt oxid and 20 "parts sodium are added theretoin portions at a time as stated in Example 1. Hydrogen is evolved andthe sodium aryl compound is formed, and can be separated in the usualmanner from the excess of mono-methyl-amin. The reaction in this exampleproceeds more slowly than in the'preceding examples.

I claim v 1. The herein described process of manufacturingsodium-aryLamins by causing so- In testimony whereof Ihave signed myname to this specification in the presence of two subscribing witnesses.

I OTTO LIEBKNEOHT. Witnesses: I

JEAN GRUND, CARL GRUND.

